LU83117A1 - Antibiotiques a noyau beta-lactame,et procede pour les preparer - Google Patents
Antibiotiques a noyau beta-lactame,et procede pour les preparer Download PDFInfo
- Publication number
- LU83117A1 LU83117A1 LU83117A LU83117A LU83117A1 LU 83117 A1 LU83117 A1 LU 83117A1 LU 83117 A LU83117 A LU 83117A LU 83117 A LU83117 A LU 83117A LU 83117 A1 LU83117 A1 LU 83117A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- amino
- radical
- salt
- group
- hydrogen atom
- Prior art date
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- 150000003952 β-lactams Chemical group 0.000 title claims description 84
- 238000004519 manufacturing process Methods 0.000 title description 9
- 239000003242 anti bacterial agent Substances 0.000 title description 8
- 229940088710 antibiotic agent Drugs 0.000 title description 7
- -1 substituent sulfonic acid salt Chemical class 0.000 claims description 350
- 150000001875 compounds Chemical class 0.000 claims description 246
- 239000000203 mixture Substances 0.000 claims description 199
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 183
- 239000002253 acid Substances 0.000 claims description 163
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 100
- 238000000034 method Methods 0.000 claims description 95
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 91
- 150000003839 salts Chemical class 0.000 claims description 70
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 58
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 55
- 229910052757 nitrogen Inorganic materials 0.000 claims description 55
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- 125000005843 halogen group Chemical group 0.000 claims description 33
- 239000000284 extract Substances 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 150000003254 radicals Chemical class 0.000 claims description 29
- 150000001412 amines Chemical class 0.000 claims description 27
- 150000001768 cations Chemical class 0.000 claims description 27
- 244000005700 microbiome Species 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- 125000003277 amino group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 238000006277 sulfonation reaction Methods 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 14
- 125000006239 protecting group Chemical group 0.000 claims description 14
- 125000004414 alkyl thio group Chemical group 0.000 claims description 13
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 12
- 241000588879 Chromobacterium violaceum Species 0.000 claims description 11
- 241000589236 Gluconobacter Species 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- 239000008103 glucose Substances 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 229920001817 Agar Polymers 0.000 claims description 9
- 239000008272 agar Substances 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229940041514 candida albicans extract Drugs 0.000 claims description 9
- ZNPKAOCQMDJBIK-UHFFFAOYSA-N nitrocyanamide Chemical compound [O-][N+](=O)NC#N ZNPKAOCQMDJBIK-UHFFFAOYSA-N 0.000 claims description 9
- 239000012138 yeast extract Substances 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- KHUNFTAJVUPPCY-UHFFFAOYSA-N azetidine-1-sulfonic acid Chemical compound OS(=O)(=O)N1CCC1 KHUNFTAJVUPPCY-UHFFFAOYSA-N 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical class CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 238000007363 ring formation reaction Methods 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- 238000005917 acylation reaction Methods 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical class [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims description 5
- 229940067157 phenylhydrazine Drugs 0.000 claims description 5
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 5
- 230000010933 acylation Effects 0.000 claims description 4
- 235000015278 beef Nutrition 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
- 150000003973 alkyl amines Chemical class 0.000 claims description 3
- 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 claims description 2
- DUAJIKVIRGATIW-UHFFFAOYSA-N trinitrogen(.) Chemical compound [N]=[N+]=[N-] DUAJIKVIRGATIW-UHFFFAOYSA-N 0.000 claims description 2
- SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 claims 9
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims 5
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 125000005907 alkyl ester group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 239000012736 aqueous medium Substances 0.000 claims 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 2
- 125000004970 halomethyl group Chemical class 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 125000005504 styryl group Chemical group 0.000 claims 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- AIRGTHIZLYPMKL-UHFFFAOYSA-N ethynylbenzene Chemical compound [C]#CC1=CC=CC=C1 AIRGTHIZLYPMKL-UHFFFAOYSA-N 0.000 claims 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 1
- 239000010931 gold Substances 0.000 claims 1
- 229910052737 gold Inorganic materials 0.000 claims 1
- BUIMWOLDCCGZKZ-UHFFFAOYSA-N n-hydroxynitramide Chemical compound ON[N+]([O-])=O BUIMWOLDCCGZKZ-UHFFFAOYSA-N 0.000 claims 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 470
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 335
- 239000000243 solution Substances 0.000 description 260
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 241
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 231
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 216
- 229910001868 water Inorganic materials 0.000 description 216
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 191
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 190
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 177
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 164
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 115
- 239000000047 product Substances 0.000 description 97
- 238000002844 melting Methods 0.000 description 90
- 230000008018 melting Effects 0.000 description 90
- 239000002904 solvent Substances 0.000 description 78
- 238000000354 decomposition reaction Methods 0.000 description 63
- 239000007787 solid Substances 0.000 description 59
- 239000003921 oil Substances 0.000 description 58
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 54
- 238000004587 chromatography analysis Methods 0.000 description 53
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 51
- 238000003756 stirring Methods 0.000 description 49
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 48
- 239000000725 suspension Substances 0.000 description 43
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 41
- 239000000706 filtrate Substances 0.000 description 41
- LVTHXRLARFLXNR-UHFFFAOYSA-M potassium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F LVTHXRLARFLXNR-UHFFFAOYSA-M 0.000 description 41
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 40
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 39
- 238000004458 analytical method Methods 0.000 description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 37
- 239000003795 chemical substances by application Substances 0.000 description 34
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 239000003480 eluent Substances 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 32
- 229940111688 monobasic potassium phosphate Drugs 0.000 description 32
- 235000019796 monopotassium phosphate Nutrition 0.000 description 32
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 32
- 235000011152 sodium sulphate Nutrition 0.000 description 32
- 238000001914 filtration Methods 0.000 description 31
- 229910052938 sodium sulfate Inorganic materials 0.000 description 31
- 239000000126 substance Substances 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 29
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 29
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 28
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 28
- 239000012043 crude product Substances 0.000 description 28
- 238000010828 elution Methods 0.000 description 28
- 239000000741 silica gel Substances 0.000 description 27
- 229910002027 silica gel Inorganic materials 0.000 description 27
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 26
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 25
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- 239000011347 resin Substances 0.000 description 24
- 229920005989 resin Polymers 0.000 description 24
- 239000003054 catalyst Substances 0.000 description 23
- 239000010410 layer Substances 0.000 description 22
- NSRVGDULUQOEBX-REOHCLBHSA-N (3s)-3-amino-2-oxoazetidine-1-sulfonic acid Chemical compound N[C@H]1CN(S(O)(=O)=O)C1=O NSRVGDULUQOEBX-REOHCLBHSA-N 0.000 description 21
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- 239000002244 precipitate Substances 0.000 description 20
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 19
- 239000012044 organic layer Substances 0.000 description 19
- 238000000746 purification Methods 0.000 description 19
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 238000005481 NMR spectroscopy Methods 0.000 description 18
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 17
- 239000002609 medium Substances 0.000 description 17
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 16
- 229910052700 potassium Inorganic materials 0.000 description 16
- 239000011591 potassium Substances 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- 238000001665 trituration Methods 0.000 description 16
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 15
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 14
- 239000004202 carbamide Substances 0.000 description 14
- 239000013256 coordination polymer Substances 0.000 description 14
- 238000001704 evaporation Methods 0.000 description 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- 239000012452 mother liquor Substances 0.000 description 14
- 239000008057 potassium phosphate buffer Substances 0.000 description 14
- 235000017557 sodium bicarbonate Nutrition 0.000 description 14
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
- 239000012298 atmosphere Substances 0.000 description 13
- 230000008020 evaporation Effects 0.000 description 13
- 239000000543 intermediate Substances 0.000 description 13
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 13
- 238000005406 washing Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000001035 drying Methods 0.000 description 12
- 230000002829 reductive effect Effects 0.000 description 12
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 11
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 11
- 238000002425 crystallisation Methods 0.000 description 11
- 230000008025 crystallization Effects 0.000 description 11
- 241000894007 species Species 0.000 description 11
- 230000003115 biocidal effect Effects 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- 238000004108 freeze drying Methods 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 150000003222 pyridines Chemical class 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- 239000011780 sodium chloride Substances 0.000 description 10
- NONZZMVLNASYPE-UHFFFAOYSA-N 3-amino-3-methoxy-2-oxoazetidine-1-sulfonic acid Chemical compound COC1(N)CN(S(O)(=O)=O)C1=O NONZZMVLNASYPE-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 9
- 229940024606 amino acid Drugs 0.000 description 9
- 229910052786 argon Inorganic materials 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 9
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- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 8
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- 229910001414 potassium ion Inorganic materials 0.000 description 1
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- PWVRQCYZCYPKFV-UHFFFAOYSA-N tert-butyl N-(2-methyl-4-oxoazetidin-1-yl)carbamate Chemical compound C(C)(C)(C)OC(=O)NN1C(CC1C)=O PWVRQCYZCYPKFV-UHFFFAOYSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- XITYBUGKVAXFSS-UHFFFAOYSA-N tert-butyl n-(2-methyl-4-oxo-1-phenylmethoxyazetidin-3-yl)carbamate Chemical compound CC1C(NC(=O)OC(C)(C)C)C(=O)N1OCC1=CC=CC=C1 XITYBUGKVAXFSS-UHFFFAOYSA-N 0.000 description 1
- PIQQONBHNFGELI-RQJHMYQMSA-N tert-butyl n-[(2r,3s)-1-methoxy-2-methyl-4-oxoazetidin-3-yl]carbamate Chemical compound CON1[C@H](C)[C@H](NC(=O)OC(C)(C)C)C1=O PIQQONBHNFGELI-RQJHMYQMSA-N 0.000 description 1
- VSTSKETWEBYEHL-RITPCOANSA-N tert-butyl n-[(2r,3s)-2-methyl-4-oxoazetidin-3-yl]carbamate Chemical compound C[C@H]1NC(=O)[C@H]1NC(=O)OC(C)(C)C VSTSKETWEBYEHL-RITPCOANSA-N 0.000 description 1
- BNHJMVYSNXQXKI-WDSKDSINSA-N tert-butyl n-[(2s,3s)-1-hydroxy-2-methyl-4-oxoazetidin-3-yl]carbamate Chemical compound C[C@H]1[C@H](NC(=O)OC(C)(C)C)C(=O)N1O BNHJMVYSNXQXKI-WDSKDSINSA-N 0.000 description 1
- XITYBUGKVAXFSS-AAEUAGOBSA-N tert-butyl n-[(2s,3s)-2-methyl-4-oxo-1-phenylmethoxyazetidin-3-yl]carbamate Chemical compound C[C@H]1[C@H](NC(=O)OC(C)(C)C)C(=O)N1OCC1=CC=CC=C1 XITYBUGKVAXFSS-AAEUAGOBSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
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- NDLIRBZKZSDGSO-UHFFFAOYSA-N tosyl azide Chemical compound CC1=CC=C(S(=O)(=O)[N-][N+]#N)C=C1 NDLIRBZKZSDGSO-UHFFFAOYSA-N 0.000 description 1
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- 208000019206 urinary tract infection Diseases 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/397—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having four-membered rings, e.g. azetidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/085—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a nitrogen atom directly attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
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- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/10—Nitrogen as only ring hetero atom
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Microbiology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11927680A | 1980-02-07 | 1980-02-07 | |
US11927680 | 1980-02-07 | ||
US18889380A | 1980-09-29 | 1980-09-29 | |
US18889380 | 1980-09-29 |
Publications (1)
Publication Number | Publication Date |
---|---|
LU83117A1 true LU83117A1 (fr) | 1982-09-10 |
Family
ID=26817179
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
LU83117A LU83117A1 (fr) | 1980-02-07 | 1981-02-06 | Antibiotiques a noyau beta-lactame,et procede pour les preparer |
Country Status (29)
Country | Link |
---|---|
JP (3) | JPS56125362A (nl) |
KR (1) | KR860001289B1 (nl) |
AR (1) | AR245932A1 (nl) |
AU (1) | AU569407B2 (nl) |
CA (1) | CA1338670C (nl) |
CH (2) | CH653993A5 (nl) |
DD (1) | DD156180A5 (nl) |
DE (1) | DE3104145C2 (nl) |
DK (1) | DK166280C (nl) |
ES (1) | ES8205397A1 (nl) |
FI (1) | FI80271C (nl) |
FR (1) | FR2509299B1 (nl) |
GB (2) | GB2071650B (nl) |
GR (1) | GR74151B (nl) |
HK (1) | HK57785A (nl) |
IE (2) | IE51393B1 (nl) |
IL (1) | IL62082A (nl) |
IT (1) | IT1135360B (nl) |
KE (1) | KE3539A (nl) |
LU (1) | LU83117A1 (nl) |
MY (1) | MY8600179A (nl) |
NL (1) | NL192924C (nl) |
NO (2) | NO161065C (nl) |
NZ (2) | NZ196202A (nl) |
PH (3) | PH24729A (nl) |
PT (1) | PT72465B (nl) |
SE (3) | SE457954B (nl) |
SG (1) | SG39185G (nl) |
YU (1) | YU44829B (nl) |
Families Citing this family (51)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0050965A1 (en) * | 1980-10-23 | 1982-05-05 | Takeda Chemical Industries, Ltd. | Beta-lactamase inhibitory composition |
WO1982001873A1 (en) * | 1980-12-05 | 1982-06-10 | Takeda Chemical Industries Ltd | 1-sulfo-2-oxoazetidine derivatives and process for their preparation |
JPS57131758A (en) * | 1980-12-05 | 1982-08-14 | Takeda Chem Ind Ltd | 1-sulfo-2-oxoazetidine derivative, its preparation and use |
US4675397A (en) * | 1980-12-05 | 1987-06-23 | Takeda Chemical Industries, Ltd. | 1-sulfo-2-oxoazetidine derivatives and their production |
JPS58210061A (ja) * | 1982-05-31 | 1983-12-07 | Takeda Chem Ind Ltd | 1−スルホ−2−オキソアゼチジン誘導体、その製造法および用途 |
US4782147A (en) * | 1980-12-05 | 1988-11-01 | Takeda Chemical Industries, Ltd. | 1-sulfo-2-oxoazetidine derivatives and their production |
WO1983000690A1 (en) * | 1981-08-25 | 1983-03-03 | Takeda Chemical Industries Ltd | Azetidine derivatives and process for their preparation |
US4673739A (en) * | 1980-12-05 | 1987-06-16 | Takeda Chemical Industries, Ltd. | 4-carbamoyloxymethyl-1-sulfo-2-oxoazetidine derivatives and their production |
MX7096E (es) * | 1980-12-05 | 1987-06-19 | Takeda Chemical Industries Ltd | Metodo para preparacion de derivados de 2-oxoazetidina |
US4572801A (en) * | 1981-04-30 | 1986-02-25 | Takeda Chemical Industries, Ltd. | 4-Carbamoyloxymethyl-1-sulfo-2-oxoazetidine derivatives and their production |
CA1181075A (en) * | 1981-07-13 | 1985-01-15 | David M. Floyd | CRYSTALLINE ANHYDROUS FORM OF [3-S-[3.alpha.(Z),4 .beta.]]-3-[[(2-AMINO-4-THIAZOLYL) [(1-CARBOXY-1-METHYLETHOXY)IMINO]ACETYL] AMINO]-4-METHYL-2-OXO-1-AZETIDINESULFONIC ACID |
FR2538389B2 (fr) * | 1981-10-23 | 1986-05-16 | Roussel Uclaf | Nouveaux produits derives de l'acide 3-amino 2-oxo azetidine-1-sulfamique, nouveau procede de preparation de produits optiquement actifs, application des nouveaux produits comme medicaments et produits necessaires a leur preparation |
FR2515182B1 (fr) * | 1981-10-23 | 1986-05-09 | Roussel Uclaf | Nouveaux produits derives de l'acide 3-amino 2-oxo azetidine 1-sulfamique, leur procede de preparation, leur application comme medicaments et les produits intermediaires necessaires a leur preparation |
IL67451A (en) * | 1981-12-25 | 1987-10-20 | Takeda Chemical Industries Ltd | 4-cyano-2-azetidinones and production thereof and process for the preparation of 4-carbamoyl-2-azetidinones using them |
EP0086563A1 (en) * | 1982-01-22 | 1983-08-24 | Beecham Group Plc | Antibacterial agents, their preparation and use |
EP0088488B1 (en) * | 1982-01-22 | 1986-10-01 | Beecham Group Plc | Antibacterial agents, their preparation and use |
US4443374A (en) * | 1982-02-01 | 1984-04-17 | E. R. Squibb & Sons, Inc. | Process for preparing (3S)-3-[[(2-amino-4-thiazolyl)[(1-carboxy-1-methylethoxy)imino]-acetyl]amino]-2-oxo-1-azetidinesulfonic acid, and 4-substituted derivatives |
WO1983002942A1 (en) * | 1982-02-19 | 1983-09-01 | Yoshioka, Kouichi | Process for preparing 2-azetidinone-1-sulfonic acids, and starting materials therefor |
AU564150B2 (en) * | 1982-04-30 | 1987-08-06 | Takeda Chemical Industries Ltd. | 1-sulfo-2-azetidinone derivatives |
EP0096297B1 (de) * | 1982-06-03 | 1988-06-15 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Verfahren zur Herstellung von 1-Sulfo-2-oxoazetidinderivaten |
EP0096296B1 (de) * | 1982-06-03 | 1987-07-29 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | 1-Sulfo-2-oxoazetidinderivate |
US4704457A (en) * | 1982-06-21 | 1987-11-03 | E. R. Squibb & Sons, Inc. | Process for the preparation of (3S)-3-[[[2-(protected amino)-4-thiazolyl]-oxoacetyl]amino]-2-oxo-1-azetidinesulfonic acid and 4-substituted derivatives thereof |
US4939253A (en) * | 1982-08-04 | 1990-07-03 | E. R. Squibb & Sons, Inc. | 2-oxoazetidin-1-yloxy acetic acids and analogs |
US4681937A (en) * | 1982-09-27 | 1987-07-21 | E. R. Squibb & Sons, Inc. | 3-acylamino-2-oxo-1-azetidinyl esters of phosphonic acids, phosphoric acid and phosphoric acid esters |
US4551276A (en) * | 1982-10-06 | 1985-11-05 | E. R. Squibb & Sons, Inc. | 2-Oxoazetidin-1-yloxymethyl sulfonic acid and analogs |
US4533495A (en) * | 1982-12-30 | 1985-08-06 | Takeda Chemical Industries, Ltd. | Method of producing 2-azetidinone-1-sulfonic acid compounds |
US4548747A (en) * | 1983-05-02 | 1985-10-22 | E. R. Squibb & Sons, Inc. | 3-Acylamino-1-sulfonylaminocarbonylmethoxy-2-azetidinones |
US4670554A (en) * | 1983-05-31 | 1987-06-02 | E. R. Squibb & Sons, Inc. | ((3-Acylamino-2-oxo-1-azetidinyl)oxy)methyl)phosphinic acids |
US4652651A (en) * | 1983-05-31 | 1987-03-24 | Hoffmann-La Roche Inc. | Process for the manufacture of 1-sulpho-2-oxoazetidine carboxylic acid intermediates via catalytic ester cleavage |
US4501697A (en) * | 1983-06-17 | 1985-02-26 | E. R. Squibb & Sons, Inc. | 4-[[(Amidomethyl)oxy]methyl]-2-oxo-1-azetidinesulfonic acid salts |
JPS601162A (ja) * | 1983-06-17 | 1985-01-07 | Dai Ichi Seiyaku Co Ltd | 3―アジド―2―オキソアゼチジン―1―スルホン酸誘導体の製造法 |
US4587051A (en) * | 1983-07-18 | 1986-05-06 | E. R. Squibb & Sons, Inc. | Desulfonation process for preparing 2-azetidinones |
US4596777A (en) * | 1983-08-10 | 1986-06-24 | E. R. Squibb & Sons, Inc. | Process for preparing (3S)-3-[[[2-(protected or unprotected amino)-4-thiazolyl]acetyl]amino]-2-oxo-1-azetidinesulfonic acid and 4-substituted derivatives thereof |
US4551277A (en) * | 1983-11-09 | 1985-11-05 | E. R. Squibb & Sons, Inc. | 4-(3-Acylamino-2-oxo-1-azetidinyl)-4-oxo-2-butenoic acid |
JPS60112789A (ja) * | 1983-11-21 | 1985-06-19 | Otsuka Chem Co Ltd | 3−アシルアミノ−4−アルキル−2−アゼチジノン−1−スルホン酸誘導体、その製造方法および該誘導体を含有する薬剤 |
JPS60226855A (ja) * | 1984-04-26 | 1985-11-12 | Nippon Kayaku Co Ltd | N−ベンジルオキシカルボニル−l−スレオニンアミド・1/2水和物およびその製造法 |
US4918185A (en) * | 1984-05-22 | 1990-04-17 | Eli Lilly And Company | Process for carbon-carbon bond formation at the C-4 position of 3-acylaminoazetidinones and products and starting materials therefor |
US4771135A (en) * | 1984-05-22 | 1988-09-13 | Eli Lilly And Company | Process for carbon-carbon bond formation at the C-4 position of 3-acylaminoazetidinones and products and starting materials therefor |
US4680409A (en) * | 1984-10-09 | 1987-07-14 | E. R. Squibb & Sons, Inc. | Hydrazide containing derivatives of 2-amino-4-thiazole-acetic acid |
US4610824A (en) * | 1984-10-09 | 1986-09-09 | E. R. Squibb & Sons, Inc. | Hydrazide derivatives of monocyclic beta-lactam antibiotics |
US4647660A (en) * | 1985-05-02 | 1987-03-03 | E. R. Squibb & Sons, Inc. | 3-acylamino-2-oxo-1-azetidinesulfonic acids |
US4632985A (en) * | 1985-06-03 | 1986-12-30 | E. R. Squibb & Sons, Inc. | 3-acylamino-2-oxo-1-azetidinesulfonic acids |
US4754041A (en) * | 1985-06-17 | 1988-06-28 | E. R. Squibb & Sons, Inc. | 3-acylamino-2-oxo-1-azetidinesulfonic acids |
US4638062A (en) * | 1985-06-17 | 1987-01-20 | E. R. Squibb & Sons, Inc. | 3-acylamino-2-oxo-1-azetidinesulfonic acids |
FR2588867B1 (fr) * | 1985-10-23 | 1988-12-09 | Roussel Uclaf | Nouveaux produits derives de la serie de la 3-amino 2-oxo azetidine, leur procede de preparation et leur application |
WO2006122253A1 (en) * | 2005-05-09 | 2006-11-16 | Sicor, Inc. | Process for making aztreonam |
JP5648250B2 (ja) * | 2007-11-21 | 2015-01-07 | 国立大学法人東京工業大学 | スルホン化含窒素複素環を有する高分子有機化合物および有機化合物、それらの製造方法、およびそれらを用いたイオン交換体、電解質膜、医薬品、触媒、膜電極接合体、燃料電池 |
WO2013109217A1 (en) | 2012-01-16 | 2013-07-25 | Mahmut Bilgic | Pharmaceutical formulations comprising aztreonam |
EP3511328B1 (en) | 2014-03-24 | 2021-03-03 | Novartis AG | Monobactam organic compounds for the treatment of bacterial infections |
PT3353175T (pt) | 2015-09-23 | 2020-09-10 | Novartis Ag | Sais e formas sólidas de um antibiótico monobactâmico |
CN111094281B (zh) | 2017-08-02 | 2023-08-29 | 诺华股份有限公司 | 用于制备单内酰胺抗生素的化学方法及其中间体 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6046955B2 (ja) * | 1977-12-30 | 1985-10-18 | 武田薬品工業株式会社 | 抗生物質g−6302 |
EP0021678B1 (en) * | 1979-06-08 | 1984-11-07 | Takeda Chemical Industries, Ltd. | 1-sulpho-2-oxoazetidine derivatives, their production and pharmaceutical compositions thereof |
JPS55164672A (en) * | 1979-06-08 | 1980-12-22 | Takeda Chem Ind Ltd | Azetidine derivative and its preparation |
WO1982001873A1 (en) * | 1980-12-05 | 1982-06-10 | Takeda Chemical Industries Ltd | 1-sulfo-2-oxoazetidine derivatives and process for their preparation |
JPS57131758A (en) * | 1980-12-05 | 1982-08-14 | Takeda Chem Ind Ltd | 1-sulfo-2-oxoazetidine derivative, its preparation and use |
-
1981
- 1981-02-05 NZ NZ196202A patent/NZ196202A/en unknown
- 1981-02-05 NZ NZ205240A patent/NZ205240A/en unknown
- 1981-02-06 FR FR8102372A patent/FR2509299B1/fr not_active Expired
- 1981-02-06 NO NO810410A patent/NO161065C/no unknown
- 1981-02-06 JP JP1737981A patent/JPS56125362A/ja active Pending
- 1981-02-06 KR KR1019810000379A patent/KR860001289B1/ko active
- 1981-02-06 DE DE3104145A patent/DE3104145C2/de not_active Expired - Lifetime
- 1981-02-06 IE IE2297/86A patent/IE51393B1/en not_active IP Right Cessation
- 1981-02-06 LU LU83117A patent/LU83117A1/fr unknown
- 1981-02-06 GB GB8103655A patent/GB2071650B/en not_active Expired
- 1981-02-06 SE SE8100861A patent/SE457954B/sv not_active IP Right Cessation
- 1981-02-06 FI FI810352A patent/FI80271C/fi not_active IP Right Cessation
- 1981-02-06 CH CH5565/84A patent/CH653993A5/de not_active IP Right Cessation
- 1981-02-06 DK DK052381A patent/DK166280C/da active
- 1981-02-06 CH CH816/81A patent/CH651020A5/de not_active IP Right Cessation
- 1981-02-06 CA CA000370320A patent/CA1338670C/en not_active Expired - Fee Related
- 1981-02-06 PH PH25195A patent/PH24729A/en unknown
- 1981-02-06 IL IL62082A patent/IL62082A/xx not_active IP Right Cessation
- 1981-02-06 PT PT72465A patent/PT72465B/pt unknown
- 1981-02-06 DD DD81227473A patent/DD156180A5/de not_active IP Right Cessation
- 1981-02-06 GR GR64081A patent/GR74151B/el unknown
- 1981-02-06 IE IE230/81A patent/IE51392B1/en not_active IP Right Cessation
- 1981-02-06 NL NL8100571A patent/NL192924C/nl not_active IP Right Cessation
- 1981-02-06 YU YU319/81A patent/YU44829B/xx unknown
- 1981-02-06 ES ES499171A patent/ES8205397A1/es not_active Expired
- 1981-02-06 IT IT19587/81A patent/IT1135360B/it active Protection Beyond IP Right Term
- 1981-02-08 AR AR81284229A patent/AR245932A1/es active
-
1983
- 1983-12-13 GB GB08333191A patent/GB2139618B/en not_active Expired
-
1984
- 1984-06-15 PH PH30820A patent/PH23317A/en unknown
- 1984-06-15 PH PH30821A patent/PH23316A/en unknown
-
1985
- 1985-05-25 SG SG391/85A patent/SG39185G/en unknown
- 1985-05-29 KE KE3539A patent/KE3539A/xx unknown
- 1985-08-01 HK HK577/85A patent/HK57785A/xx not_active IP Right Cessation
- 1985-08-02 AU AU45748/85A patent/AU569407B2/en not_active Expired
-
1986
- 1986-01-22 NO NO86860225A patent/NO170015C/no unknown
- 1986-05-14 SE SE8602193A patent/SE500216C2/sv unknown
- 1986-05-14 SE SE8602194A patent/SE8602194L/xx not_active Application Discontinuation
- 1986-12-30 MY MY179/86A patent/MY8600179A/xx unknown
-
1989
- 1989-11-22 JP JP1304538A patent/JPH0623188B2/ja not_active Expired - Lifetime
-
1991
- 1991-05-27 JP JP3121251A patent/JPH0670006B2/ja not_active Expired - Lifetime
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